WO2014126208A1 - Polymorphe cristallin de composé de benzamide substitué par isoxazoline et son procédé de production - Google Patents

Polymorphe cristallin de composé de benzamide substitué par isoxazoline et son procédé de production Download PDF

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WO2014126208A1
WO2014126208A1 PCT/JP2014/053507 JP2014053507W WO2014126208A1 WO 2014126208 A1 WO2014126208 A1 WO 2014126208A1 JP 2014053507 W JP2014053507 W JP 2014053507W WO 2014126208 A1 WO2014126208 A1 WO 2014126208A1
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crystal
compound
crystals
crystalline polymorph
dispersion medium
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PCT/JP2014/053507
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English (en)
Japanese (ja)
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義之 楠岡
雅仁 堀
紘久 齋藤
水越　隆司
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日産化学工業株式会社
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Priority to CN201480005009.XA priority Critical patent/CN105121416B/zh
Priority to JP2015500314A priority patent/JPWO2014126208A1/ja
Publication of WO2014126208A1 publication Critical patent/WO2014126208A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

  • the present invention relates to (Z)-[5- (3,5-dichlorophenyl) -5-trifluoromethyl-4,5-dihydroisoxazol-3-yl] -N- (methoxyiminomethyl) -2-methyl
  • the present invention relates to a crystalline polymorph of benzoic acid amide (hereinafter referred to as Compound A), a production method thereof, and a suspension composition containing the crystalline polymorph of Compound A.
  • the solid state of the chemical compound can be amorphous (ie, there is no long range order at the position of the atoms) or crystalline (ie, the atoms are arranged in an ordered repeating pattern). Only a single crystal form is known for the solid state of many compounds, but polymorphs have been found for some compounds.
  • polymorph refers to a specific crystal form of a chemical compound (ie, the structure of a crystal lattice) that can exist in two or more crystal forms in the solid state.
  • the pest control agent in the present invention refers to the field of agriculture and horticulture or the field of animal husbandry / hygiene (a mammal or avian or domestic parasite control agent for domestic animals or pets, hygiene pests or unpleasant pests for household or commercial use. It means a pest control agent for harmful arthropods such as (control agent).
  • the object of the present invention is to provide a novel crystalline polymorph of Compound A and a process for its preparation. Another object of the present invention is to provide a suspension composition containing Compound A and having improved storage stability.
  • the present invention relates to the following [1] to [17].
  • diffraction angles 2 ⁇ (5.00 ⁇ 0.2, 9.24 ⁇ 0.2, 13.39 ⁇ 0.2, 16.45 ⁇ 0.2, 19.
  • a suspension composition containing the I-form crystal of [1] and a dispersion medium [10] A suspension composition containing the I-form crystal of [1] and a dispersion medium. [11] An aqueous suspension composition containing water as a I-form crystal, a surfactant and a dispersion medium as described in [1] above. [12] A suspension composition containing the type II crystal and the dispersion medium as described in [3] above. [13] An aqueous suspension composition containing water as a type II crystal, a surfactant and a dispersion medium as described in [3] above.
  • the crystalline polymorph of compound A can be controlled.
  • the suspension composition containing the compound A of the present invention has good storage stability, and the suspension particles of the compound A are prevented from growing over time. The problem of a decrease in pest control activity due to the growth of the plant does not occur.
  • Example 2 shows a powder X-ray diffraction chart of type I crystal. 2 shows a powder X-ray diffraction chart of type II crystal.
  • Example 4 the powder X-ray-diffraction chart of the dried compound A taken out from the aqueous suspension agricultural chemical composition immediately after manufacture is shown.
  • Example 17 the powder X-ray-diffraction chart of the dried compound A taken out from the aqueous suspension agricultural chemical composition immediately after manufacture is shown.
  • Compound A is (Z)-[5- (3,5-dichlorophenyl) -5-trifluoromethyl-4,5-dihydroisoxazol-3-yl] -N- (methoxyiminomethyl) -2-methyl Benzoic acid amide.
  • the molecular structure of Compound A can exist as two different stereoisomers (ie enantiomers). However, the present invention relates to a racemic mixture of Compound A comprising equal amounts of these two possible enantiomers.
  • Compound A may contain an E geometric isomer derived from an iminomethyl structure as an impurity.
  • Table 1 shows the powder X-ray diffraction peaks as the characteristics of Compound I Form I and Form II crystals.
  • the peak value of the I-form crystal described in Table 1 is an average value of the peak values of the 7 lot I-form crystals obtained according to the method described in the following examples.
  • the peak value of the II type crystal described in Table 1 is the average value of the peak values of the six lots of the II type crystal as in the case of the I type crystal.
  • the Form I crystal of Compound A can be produced by the following method.
  • Compound A is dissolved in a solvent by heating and the resulting solution is gradually cooled and crystallized, or by distilling off the solvent from the resulting solution and crystallizing. Crystals are obtained.
  • the solvent to be used may be any solvent inert to the compound A.
  • diethyl ether methyl t-butyl ether, tetrahydrofuran, dimethoxymethane, diethoxymethane, ethylene glycol dimethyl ether, ethylene Ether systems such as glycol diethyl ether, ethylene glycol dibutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, 1,4-dioxane, etc.
  • ethylene Ether systems such as glycol diethyl ether, ethylene glycol dibutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, 1,4-dioxane, etc.
  • Solvent methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, isobutanol, 2-methyl-2-propanol, methyl cellosolve , Ethyl cellosolve, i-propyl cellosol Alcohol solvents such as diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, cyclohexanol, benzyl alcohol, pentane, hexane, cyclohexane, methylcyclohexane, heptane, octane, decane Aliphatic hydrocarbon solvents such as benzene, toluene, xylene, chlorobenzene, o-dichlorobenzene, m-dichlorobenzene, p-dichlorobenzene, nitrobenzene, tetrahydronaphthalene and the like
  • solvents can be used and these solvents can be used individually or in mixture of 2 or more types.
  • these solvents aliphatic hydrocarbon solvents, aromatic hydrocarbon solvents or nitrile solvents are preferable, and heptane, xylene, toluene or acetonitrile is more preferable.
  • the amount of the solvent used is usually 0.5 to 50 parts by weight, preferably 1 to 30 parts by weight with respect to 1 part by weight of Compound A.
  • the temperature at which compound A is dissolved in the solvent is usually 30 to 150 ° C., preferably 30 to 100 ° C.
  • the cooling rate is usually 0.1 to 40 ° C./hour, preferably 1 to 30 ° C./hour, and can be changed to any cooling rate within the above range at any time.
  • the temperature of the solution when taking out the precipitated crystals is usually ⁇ 30 to 50 ° C., preferably ⁇ 20 to 30 ° C.
  • the time required for crystallization is usually 0.1 to 100 hours, preferably 1 to 50 hours.
  • the solvent when the solvent is distilled off, the solvent can be distilled off by heating to the boiling point of the solvent or higher under atmospheric pressure. Moreover, the solvent can be distilled off at an arbitrary temperature up to the boiling point of the solvent under reduced pressure by adjusting the degree of vacuum in the container.
  • Compound A type II crystals can be produced by the following method.
  • a compound A is heated and dissolved in a solvent, and the resulting solution of compound A is dissolved in a low-temperature solvent.
  • Form II of crystals of compound A is obtained by a method in which the solution is dropped and crystallized, or a method in which compound A is heated and dissolved in a solvent and a low-temperature solvent is dropped therein.
  • the solvent that can be used in preparing the solution of Compound A may be any solvent that is inert with respect to Compound A.
  • aromatic hydrocarbon solvents aromatic hydrocarbon solvents, nitrile solvents or ester solvents are preferable, and xylene, toluene, acetonitrile, ethyl acetate or butyl acetate is more preferable.
  • the amount of the solvent used for dissolving the compound A is usually 0.5 to 50 parts by weight, preferably 1 to 30 parts by weight with respect to 1 part by weight of the compound A.
  • the low-temperature solvent may be any solvent that is inert with respect to Compound A.
  • -Tell solvents methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, isobutanol, 2-methyl-2-propanol , Methyl cellosolve, ethyl cellosolve, i-propyl Alcohol solvent such as rosolve, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, cyclohexanol, benzyl alcohol, pentane, hexane, cyclohexane, methylcyclohexane, heptane, octane, Aliphatic hydrocarbon solvents such as decane, aromatic hydrocarbon solvents such as benzene, toluene, xylene, chlorobenzene, o-dichlorobenzene, m-dichlorobenzene, p-dichlorobenzene, nitro
  • aliphatic hydrocarbon solvents aliphatic hydrocarbon solvents, aromatic hydrocarbon solvents or nitrile solvents are preferable, and heptane, xylene, toluene or acetonitrile is more preferable.
  • the low-temperature solvent may be the same as or different from the solvent that dissolves the compound.
  • the amount used in the case of using a low-temperature solvent is usually 1 to 100 parts by weight, preferably 5 to 50 parts by weight with respect to 1 part by weight of Compound A.
  • the speed at which the solution containing Compound A is rapidly cooled is usually 40 ° C./hour or more.
  • the temperature of the low temperature solvent is usually ⁇ 30 to 50 ° C., preferably ⁇ 20 to 30 ° C.
  • the temperature of the solution when taking out the precipitated crystals is usually ⁇ 30 to 50 ° C., preferably ⁇ 20 to 30 ° C.
  • Form I crystal of Compound A can be obtained by converting the Form II crystal of Compound A according to the method described below.
  • Suspension method A solid form of compound A containing Form II crystals is charged into a dispersion medium, and the resulting suspension is allowed to stand or stir for a certain period of time to obtain Form I crystals of Compound A.
  • the dispersion medium the solvent used in the production of the above-mentioned type I crystal can be used.
  • these dispersion media aromatic hydrocarbons or nitriles are preferable, and xylene, toluene, or acetonitrile is particularly preferable.
  • the temperature of the suspension during standing or stirring is usually -20 to 100 ° C.
  • the standing or stirring time is preferably as long as possible. Usually, the standing or stirring is performed for 1 hour or longer.
  • Crystallization method + suspension method In the above crystallization method, when a mixture of Form I and Form II crystals of Compound A is obtained, the resulting suspension is converted to Form I crystals by standing or stirring for a certain period of time. Can do.
  • (3) Heating method By heating Compound A in solid state containing Form II crystals, it can be converted to Form I crystals. Examples of the heating method include a method by contact with a high-temperature inert gas, and a method of mixing with a mixer equipped with a heating device. It can also be converted to Form I crystals by heating a suspension of Compound A Form II crystals or a mixture of Form II crystals and Form I crystals.
  • a solid suspension containing Compound A Form II crystals can be converted to Form I crystals by wet milling.
  • As the wet pulverizer an in-line mill or a bead mill can be used.
  • Dry grinding method A solid containing Compound II Form II crystals can be converted to Form I crystals by dry milling.
  • As the dry pulverizer a hammer mill, a pin mill, a jet mill, a ball mill, a roll mill, or the like can be used.
  • Each of the Form I crystals and Form II crystals of Compound A has technical characteristics such as not only improvement in formulation stability but also improvement in activity and ease of handling.
  • water or an organic liquid in which compound A is difficult to dissolve can be used as the dispersion medium.
  • the organic liquid include alcohols such as ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol and isopropanol, ethers such as butyl cellosolve, ketones such as cyclohexanone, esters such as ⁇ -butyrolactone, N-methylpyrrolidone and N-octyl.
  • Acid amides such as pyrrolidone, aromatic hydrocarbons such as xylene, alkylbenzene, phenylxylylethane and alkylnaphthalene, aliphatic hydrocarbons such as machine oil, normal paraffin, isoparaffin and naphthene, aromatic hydrocarbons such as kerosene and aliphatic Fats and oils such as a mixture of hydrocarbons, soybean oil, linseed oil, rapeseed oil, coconut oil, cottonseed oil and castor oil can be mentioned.
  • the content of Form I crystals and / or Form II crystals of Compound A is usually 0.1 to 50 parts by weight, more preferably 1 to 30 parts by weight with respect to 100 parts by weight of the composition of the present invention.
  • the growth of the suspended particles of Compound A over time is suppressed.
  • the suspension composition containing Compound A having a content of Form I crystals of 50 to 100% by weight also suppresses the growth of Compound A suspension particles over time.
  • the suspension composition containing Compound A type II crystals suppresses the growth of Compound A suspension particles over time.
  • the suspension composition containing Compound A having a content of Form II crystals of 99.9 to 100% by weight also suppresses the growth of suspended particles of Compound A over time.
  • composition of the present invention may also contain one or more other known agricultural chemicals such as herbicides, insecticides, acaricides, nematicides, antiviral agents, plant growth regulators, fungicides, A synergist, an attractant, a repellent, and the like may be contained, and in this case, a more excellent control effect may be exhibited.
  • agrochemicals are fungicides, bactericides, nematicides, acaricides and insecticides.
  • Specific examples of common names are as follows, but the general names are not necessarily limited thereto.
  • Bactericides acibenzolar-S-methyl, acylaminobenzamide, acypetacs, aldimorph, ametoctradin, amisulbrom, amobam, ampropyl Phos (ampropyfos), anilazine, azaconazole, azithiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M (benalaxyl-M), benodanil, benomyl, benquinox, bentaluron, benthiavalicarb, benthiazole, benzamacril, benzamorf, bethoxazine, benaxal, (Binapacryl Biphenyl, bitertanol, blasticidin-S, bixafen, bordeauxdemixture, boscalid, bromoconazole, bupirimate, Buthiobate, calcium polysulfide, calcium
  • Bactericides (continued): diethofencarb, difenoconazole, diflumetorim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole-, diniconazole-M M), dinobuton, dinocap, dinocap-4, dinocap-6, dinoton, dinosulfon, dinoterbon, diphenylamine ), Dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon, edifenphos, epoxiconazole, ethaconazole, etaconazole Boxaam, etem, etirimol, ethoxyquin, etridiazole, famoxadone, fenarimol, febuconazole, fenamidone, sulfaminosulfen ), Fenapanil, fendazo
  • Fungicide (continued): kasugamycin, kresoxim-methyl, mancopper, mancozeb, mandipropamid, maneb, mebenil, mecarbinzid , Mepanipyrim, mepronil, metalaxyl, metalaxyl-M, metam, metazoxolon, metconazole, methasulfocarb, metoxafloxam ), Methylisothiocyanate, metiram, metinominostrobin, metrafenone, metsulfovax, milneb, microbutanil, microzoline (myc) lozolin, nabam, natamycin, nickel bis (dimethyldithiocarbamate), nitrostyrene, nitrothal-isopropyl, nuarimol, OH (OCH), octhilinone, offurace, orysastrobin, oxadixyl, organic copper (oxi
  • Bactericides (continued): sodium azide, sodium hydrogen carbonate, sodium hypopochlorite, sulfur, spiroxamine, salicylanilide, silthiofam ( silthiofam, simeconazole, tebuconazole, tecnazene, tecoram, tetraconazole, thiabendazole, thiadifluor, thicyofen, fluzamide th ), Thiochlorfenphim, thiophanate, thiophanate-methyl, thioquinox, thiram, tiadinil, thiooxymid, tolcrofos Methyl (tolclofos-methyl), tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol, triazoxide, triazbutil, tributyltin oxide (tributyltin oxide) ), Trichlamide, tricyclazole, tridemorph,
  • Bactericides benzalkonium chloride, bithionol, bronopol, cresol, formaldehyde, nitrapyrin, oxolinic acid, oxyterracycline , Streptomycin and tecloftalam.
  • Nematicides aldoxycarb, cadusafos, DCP, DBCH, dichlofenthion, DSP (DSP), etoprophos, fenamiphos, fensulfothion, fluene Sulfone (fluensulfone), fosthiazate (fosthiazate), fosthietan (fosthietan), imisiafos (imicyafos), isamidofos (isamidofos), isazofos (isazofos), oxamyl (oxamyl) and thionazin (thionazin).
  • Acaricides acequinocyl, acrinathrin, amitraz, BCI-033 (test name), bifenazate, bromopropylate, chinomethionat, chlorobezilate , Clofentezine, cyenopyrafen, cyflumetofen, cyhexatine, dicofol, dienochlor, denochlor (DNOC), etoxazole, quinazaquin (fenaza) Fenbutatin oxide, phenothiocarb, fenpropathrin, fenpyroximate, fluacrypyrim, halfenprox (halfe) nprox), hexythiazox, milbemectin, propargite, pyridaben, pyrimidifen, S-1870 (test name), spirodiclofen, spiromesifen ( spyromesifen), NNI-0711 (test name), CL900137 (test name)
  • Insecticides abamectin, acephate, acetamipirid, alanamicarb, aldicarb, allethrin, azamethiphos, azinphos-methyl, bacillus turin Bacillus thuringiensis, bendiocarb, benfluthrin, benfuracarb, bensultap, bifenthrin, bioallethrin, bioresmethrin, bistrifluron Buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, carbosulfan, cartap, chlorantraniliprole Chlorethoxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos-methyl, chromafenozide (chromafenozide) ), Clothianidin, cyantraniliprole, cyclo
  • Insecticides (continued): halofenozide, hexaflumuron, hydramethylnon, imidacloprid, isofenphos, indoxacarb, isoprocarb, isoxathion ), Lepimectin, lufenuron, malathion, meperfluthrin, metaflumizone, metalaldehyde, methamidophos, methidathion, methidathion, methacrifos (methacrifos) ), Metalcarb, methomyl, methoprene, methoxychlor, methoxyfenozide, methyl bromi de), monocrotophos, muscalure, nitenpyram, novaluron, noviflumuron, omethoate, oxamyl, oxydemeton-methyl, oxydeproton Phos (oxydeprofos), parathion, parathion-methyl
  • a surfactant can be added as necessary.
  • these surfactants include the following (A), (B), (C), (D), and (E).
  • Nonionic surfactant (A-1) Polyethylene glycol surfactants: for example, polyoxyethylene alkyl (for example C 8 ⁇ 18) ether, ethylene oxide adducts of alkyl naphthol, polyoxyethylene (mono or di) alkyl (e.g.
  • C 8 ⁇ 12 ) phenyl ether polyoxyethylene (mono- or di-) alkyl (for example C 8 ⁇ 12) formalin condensates of phenyl ether, polyoxyethylene (mono-, di- or tri-) phenyl phenyl ether, polyoxyethylene (mono-, di- or tri ) Benzyl phenyl ether, polyoxypropylene (mono, di or tri) benzyl phenyl ether, polyoxyethylene (mono, di or tri) styryl phenyl ether, polyoxypropylene (mono, di or tri) styryl phenyl ether, polyoxy Ethylene (mono-, di- or tri-) styryl phenyl ether polymer, polyoxyethylene polyoxypropylene (mono-, di- or tri-) styryl phenyl ether, polyoxyethylene polyoxypropylene block polymers, alkyl (e.g.
  • C 8 ⁇ 18) monoesters polyoxyethylene fatty acid (e.g. C 8 ⁇ 18) diesters, polyoxyethylene sorbitan (mono-, di- or tri) fatty acid (e.g. C 8 ⁇ 18) Ester, glycerol fatty acid ester ethylene oxide adduct, castor oil ethylene oxide adduct, hydrogenated castor oil ethylene oxide adduct, alkyl (e.g., C 8 ⁇ 18) amine ethylene oxide adduct and a fatty acid (e.g. C 8 ⁇ 18) amide ethylene oxide Additives etc.
  • A-2 a polyhydric alcohol type surfactants: For example, glycerol fatty acid esters, polyglycerol fatty acid esters, pentaerythritol fatty acid esters, sorbitol fatty acid (e.g. C 8 ⁇ 18) ester, sorbitan (mono-, di- or tri) fatty acid ( For example C 8 ⁇ 18) esters, sucrose fatty acid esters, polyhydric alcohol alkyl ethers, alkyl glycosides, alkyl polyglycosides and fatty acid alkanolamides and the like.
  • glycerol fatty acid esters For example, glycerol fatty acid esters, polyglycerol fatty acid esters, pentaerythritol fatty acid esters, sorbitol fatty acid (e.g. C 8 ⁇ 18) ester, sorbitan (mono-, di- or tri) fatty acid ( For example C 8 ⁇ 18) est
  • Acetylene-based surfactant For example, acetylene glycol, acetylene alcohol, ethylene oxide adduct of acetylene glycol, ethylene oxide adduct of acetylene alcohol, and the like.
  • (B) Anionic surfactant (B-1) Carboxylic acid type surfactant: for example, polyacrylic acid, polymethacrylic acid, polymaleic acid, polymaleic anhydride, maleic acid or maleic anhydride and olefin (for example, isobutylene and diisobutylene) Polymer, Copolymer of acrylic acid and itaconic acid, Copolymer of methacrylic acid and itaconic acid, Copolymer of maleic acid or maleic anhydride and styrene, Copolymer of acrylic acid and methacrylic acid, Acrylic acid a copolymer of acrylic acid methyl ester, a copolymer of acrylic acid and vinyl acetate, a copolymer of acrylic acid and maleic acid or maleic anhydride, polyoxyethylene alkyl (for example C 8 ⁇ 18) ether acetic acid, N- methyl - fatty acids (e.g., C 8 ⁇ 18) sarcosinates,
  • (B-2) sulfate surfactants for example, alkyl (e.g., C 8 ⁇ 18) sulfates, polyoxyethylene alkyl (for example C 8 ⁇ 18) ether sulfuric acid ester, polyoxyethylene (mono or di) alkyl ( for example C 8 ⁇ 12) phenyl ether sulfuric acid ester, polyoxyethylene (mono or di) alkyl (e.g.
  • (B-3) a sulfonic acid type surfactants:
  • paraffins for example C 8 ⁇ 22
  • alkyl e.g., C 8 ⁇ 12
  • alkyl e.g., C 8 ⁇ 12
  • formalin benzenesulfonic acid condensates formalin condensates of cresol sulfonic acid
  • alpha-olefins e.g., C 8 ⁇ 16
  • dialkyl eg C 8 ⁇ 12
  • phenyl ether sulfonate polyoxyethylene alkyl (for example C 8 ⁇ 18) ether sulfosuccinic acid half ester, naphthalene sulfonic acid, (mono or di) alkyl (e.g. C 1 ⁇ 6) naphthalenesulfonic acid, naphthalenesulfonic Acid formalin condensate (mono or ) Alkyl (e.g.
  • (B-4) phosphoric acid ester type surfactants For example, alkyl (e.g., C 8 ⁇ 12) phosphates, polyoxyethylene alkyl (for example C 8 ⁇ 18) ether phosphate esters, polyoxyethylene (mono- or di-) alkyl ( for example C 8 ⁇ 12) phenyl ether phosphate ester, a polyoxyethylene (mono-, di- or tri) alkyl (e.g.
  • phosphoric acid esters of C 8 ⁇ 12) phenyl ether polymer polyoxyethylene (mono-, di- or tri-) phenyl phenyl ether Phosphate ester, polyoxyethylene (mono, di or tri) benzyl phenyl ether phosphate ester, polyoxyethylene (mono, di or tri) styryl phenyl ether phosphate ester, polyoxyethylene (mono, di or tri) styryl phenyl ether polymer
  • the phosphoric acid beauty treatment salon Phosphoric acid esters of polyoxyethylene polyoxypropylene block polymers, phosphoric acid esters such as phosphatidylcholine, phosphatidylethanolimine and condensed phosphoric acid (such as tripolyphosphoric acid), and salts of these phosphoric acid esters.
  • the counter ions of the salts in the above (B-1) to (B-4) include alkali metals (such as lithium, sodium and potassium), alkaline earth metals (such as calcium and magnesium), ammonium and various amines (eg, alkyl) Amine, cycloalkylamine, alkanolamine, etc.).
  • Cationic surfactant For example, alkyl amines, alkyl quaternary ammonium salts, ethylene oxide adducts of alkyl amines and ethylene oxide adducts of alkyl quaternary ammonium salts.
  • (D) Amphoteric surfactant (D-1) Betaine-type surfactants: For example, alkyl (e.g., C 8 ⁇ 18) betaine, acyl (e.g., C 8 ⁇ 18) aminopropyl acid betaine, alkyl (e.g., C 8 ⁇ 18) hydroxy sulfo betaine and 2-alkyl (e.g. C 8 ⁇ 18) -N- carboxymethyl -N- hydroxyethyl imidazolinium betaine
  • (D-2) amino acid-type surfactants For example, alkyl (e.g., C 8 ⁇ 18) aminopropionic acid, an alkyl (e.g., C 8 ⁇ 18) aminodipropionate acid and N- acyl (e.g. C 8 ⁇ 18) -N And '-carboxyethyl-N'-hydroxyethylethylenediamine.
  • alkyl e.g., C 8 ⁇ 18 aminopropionic acid
  • an alkyl e.g., C 8 ⁇ 18 aminodipropionate acid
  • N- acyl e.g. C 8 ⁇ 18
  • Amine oxide-type surfactants For example, alkyl (e.g., C 8 ⁇ 18) dimethyl amine oxides and acyl (e.g. C 8 ⁇ 18) aminopropyl dimethyl amine oxide, and the like.
  • (E) Other surfactants (E-1) Silicone surfactants: for example, polyoxyethylene / methylpolysiloxane copolymer, polyoxypropylene / methylpolysiloxane copolymer, and poly (oxyethylene / oxypropylene) / methylpolysiloxane copolymer Etc.
  • Fluorosurfactant For example, perfluoroalkenyl benzene sulfonate, perfluoroalkyl sulfonate, perfluoroalkyl carboxylate, perfluoroalkenyl polyoxyethylene ether, perfluoroalkyl polyoxyethylene ether And perfluoroalkyltrimethylammonium salt.
  • surfactants can be used alone or in admixture of two or more, and the ratio in the case of mixing can also be freely selected.
  • content of this surfactant in this invention composition can be selected suitably, the range of 0.1-20 weight part is preferable with respect to 100 weight part of this invention composition.
  • composition of the present invention can further contain various adjuvants.
  • auxiliary agents that can be used include thickeners, organic solvents, antifreezing agents, antifoaming agents, antibacterial and antifungal agents, coloring agents, and the like.
  • the thickener is not particularly limited, and organic, inorganic natural products, synthetic products, and semi-synthetic products can be used.
  • heteropolysaccharides such as xanthan gum (xanthan gum), welan gum and rhamzan gum, polyvinyl alcohol, polyvinyl Water-soluble polymer compounds such as pyrrolidone, polyacrylic acid, sodium polyacrylate and polyacrylamide, cellulose derivatives such as methylcellulose, carboxymethylcellulose, carboxyethylcellulose, hydroxyethylcellulose and hydroxypropylcellulose, montmorillonite, saponite, hectorite, bentonite and laponite And smectite clay minerals such as synthetic smectites.
  • thickeners may be used alone or in combination of two or more, and the ratio in the case of mixing can be freely selected. These thickeners may be added as they are, or those previously dispersed in water may be added. Moreover, content in this invention composition can also be selected freely.
  • organic solvent examples include alcohols such as ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol and isopropanol, ethers such as butyl cellosolve, ketones such as cyclohexanone, esters such as ⁇ -butyrolactone, N-methylpyrrolidone and N-octylpyrrolidone.
  • Aromatic hydrocarbons such as acid amides such as xylene, alkylbenzene, phenylxylylethane and alkylnaphthalene, aliphatic hydrocarbons such as machine oil, normal paraffin, isoparaffin and naphthene, aromatic hydrocarbons such as kerosene and aliphatic carbonization Examples include fats and oils such as a mixture of hydrogen, soybean oil, linseed oil, rapeseed oil, coconut oil, cottonseed oil and castor oil.
  • antifreezing agent for example, ethylene glycol, diethylene glycol, propylene glycol, glycerin and the like can be used. Preferred are propylene glycol and glycerin. Moreover, content in this invention composition can also be selected freely.
  • an antifoaming agent such as a silicone-based emulsion, an antibacterial and antifungal agent, a coloring agent, and the like may be added.
  • the method for producing the composition of the present invention is not particularly limited, and can be obtained by adding the above-described components to a dispersion medium and mixing with a stirrer. If necessary, the pesticidal active ingredient, surfactant and other auxiliary agents may be singly or mixed and finely pulverized by a dry type and a wet type pulverizer.
  • Dry pulverization can be performed with a hammer mill, pin mill, jet mill, ball mill, roll mill or the like.
  • the fine pulverization by wet pulverization can be performed by a wet pulverizer such as an in-line mill or a bead mill.
  • composition of the present invention is diluted by about 50 to 5000 times with, for example, a stock solution or water, and sprayed onto a crop or tree or soil where it grows using a sprayer or the like, using a helicopter from the air, etc. It can be applied by diluting with a stock solution or water about 2 to 100 times and spraying.
  • High performance liquid chromatography (HPLC), powder X-ray diffraction and DSC measurement (differential scanning calorimetry) in the examples were performed under the measurement conditions shown below.
  • Example 1 Preparation of a crystalline polymorph of Compound A, designated as Form I 4- [5- (3,5-dichlorophenyl) -5-trifluoromethyl-4,5-dihydroisoxazole-3 A solution of 2.00 g of -yl] -2-methylbenzoic acid amide, 4.26 g of triethyl orthoformate and 0.60 g of methoxyamine hydrochloride in 10 ml of toluene was stirred at 35 ° C for 24 hours. After stirring, 10 ml of toluene was added to the reaction solution. After completion of the addition, the reaction solution was heated to 60 to 65 ° C. and washed with water (4 ml ⁇ 3 times).
  • the toluene solution obtained after washing with water was analyzed by HPLC.
  • the relative area percentage of the peak derived from the main product was 90.4%.
  • the relative area percentage of the derived peak was 3.4%.
  • toluene solution 10 ml of toluene was distilled off under reduced pressure. After the distillation, the toluene solution was cooled from about 70 ° C. at a rate of about 20 ° C./hour. After crystals were formed in the toluene solution, the solution was stirred at 0 to 5 ° C. for 3 hours. After the stirring, the precipitated crystals were taken out by filtration under reduced pressure, and the obtained crystals were dried under reduced pressure to obtain 1.92 g of white crystals.
  • the relative area percentage of the peak derived from the main product was 93.0%, and the relative area percentage of the peak derived from the by-product was 3.3%. It was.
  • Supporting Information include a chemical shift value of a peak derived from a hydrogen atom on a nitrogen atom of an amide structure in a compound similar to the structure of Compound A (hereinafter referred to as amide). And a chemical shift value of a peak derived from a hydrogen atom on a carbon atom of an iminomethyl structure (hereinafter, referred to as a chemical shift value of iminomethyl).
  • amide a chemical shift value of a peak derived from a hydrogen atom on a carbon atom of an iminomethyl structure
  • iminomethyl a chemical shift value of iminomethyl
  • the diffraction pattern of FIG. As a result of measuring powder X-ray diffraction of the obtained white crystal, the diffraction pattern of FIG. Moreover, as a result of performing DSC measurement of the obtained crystal, the peak top showed an endothermic peak of 171.2 ° C., and no endothermic peak was observed at other temperatures.
  • the solution was stirred for 5 minutes under ice cooling. After completion of the stirring, the crystals precipitated in the solution were taken out by filtration under reduced pressure, and the obtained crystals were dried under reduced pressure to obtain 0.45 g of white crystals.
  • Example 1 As a result of measuring powder X-ray diffraction of the obtained crystal, it was found that a crystal completely different from the crystal obtained in Example 1 was obtained, showing the diffraction pattern of FIG. Named. Further, when DSC measurement was performed on the obtained crystal, the peak top showed an endothermic peak of 164.3 ° C., and no endothermic peak was shown at other temperatures.
  • the relative area percentage of compound A was 97.3%, and the relative area percentage of E-form of compound A was 2.5%. Further, as a result of measuring the powder X-ray diffraction of the obtained crystal, it was found that it was an I-type crystal showing substantially the same pattern as FIG.
  • dispersion medium In 19.55 parts of water, 0.05 part of 1,2-benzisothiazolin-3-one (trade name: PROXEL GXL, manufactured by Avisia), xanthan gum (trade name: KELZAN ASX, manufactured by CP Kelco) ) 0.1 part and 0.3 part of smectite clay (trade name: VEEGUM R, manufactured by RT Vanderbilt) were dispersed in this order to obtain 20 parts of a dispersion medium.
  • PROXEL GXL manufactured by Avisia
  • xanthan gum trade name: KELZAN ASX, manufactured by CP Kelco
  • smectite clay trade name: VEEGUM R, manufactured by RT Vanderbilt
  • aqueous suspension pesticide composition 80 parts of the pulverized slurry and 20 parts of dispersion medium were mixed to obtain 100 parts of a uniform aqueous suspension pesticide composition.
  • the obtained sediment was spread on a filter paper and dried in a desiccator.
  • the diffraction pattern of FIG. 4 was shown and the diffraction pattern substantially the same as FIG. 2 was shown. That is, no transition of Form II crystals was observed at the stage of preparation of the aqueous suspension pesticide composition.
  • aqueous suspension pesticide composition Immediately after the production of the obtained aqueous suspension pesticide composition, and after placing them in an 8 ml vial, the particle diameter was measured after storage in a thermostatic bath at 54 ° C. for 14 days. The average particle size was measured under the following measurement conditions.
  • Model name Particle size distribution analyzer LS-13320 manufactured by Beckman Coulter Measurement method: Laser diffraction scattering method The results are shown in Table 2. However, “%” means% by weight.
  • the suspension composition containing the crystal form has good storage stability and is useful as a pest control agent.

Abstract

L'invention a pour but de proposer : une forme cristalline de l'amide d'acide (Z)-[5-(3,5-dichlorophényl)-5-trifluorométhyl-4,5-dihydroisoxazol-3-yl]-N-(méthoxyiminométhyl)-2-méthyl-benzoïque ; un procédé de production de la forme cristalline ; et une composition de type suspension contenant la forme cristalline. A cet effet, l'invention concerne un cristal de type I ou de type II de l'amide d'acide (Z)-[5-(3,5-dichlorophényl)-5-trifluorométhyl-4,5-dihydroisoxazol-3-yl]-N-(méthoxyiminométhyl)-2-méthyl-benzoïque ; une composition de type suspension contenant le cristal de type I et un milieu de dispersion et ayant une bonne stabilité de stockage ; et une composition de type suspension contenant le cristal de type II et un milieu de dispersion et ayant une bonne stabilité de stockage.
PCT/JP2014/053507 2013-02-14 2014-02-14 Polymorphe cristallin de composé de benzamide substitué par isoxazoline et son procédé de production WO2014126208A1 (fr)

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Cited By (70)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015115488A1 (fr) * 2014-01-31 2015-08-06 日産化学工業株式会社 Composition de pesticide liquide
WO2016071499A1 (fr) 2014-11-06 2016-05-12 Basf Se Composé hétérobicyclique de 3-pyridyle utilisé pour lutter contre les invertébrés nuisibles
WO2016128261A2 (fr) 2015-02-11 2016-08-18 Basf Se Mélange pesticide comprenant un composé pyrazole, un insecticide et un fongicide
WO2016162371A1 (fr) 2015-04-07 2016-10-13 Basf Agrochemical Products B.V. Utilisation d'un composé de carboxamide insecticide contre les nuisibles sur des plantes cultivées
WO2016198611A1 (fr) 2015-06-11 2016-12-15 Basf Se Composés hétérocycliques n-(thio)acylimino
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WO2017016883A1 (fr) 2015-07-24 2017-02-02 Basf Se Procédé de préparation de composés cyclopentène
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WO2017153218A1 (fr) 2016-03-11 2017-09-14 Basf Se Procédé pour lutter contre des organismes nuisibles aux végétaux
WO2017153217A1 (fr) 2016-03-09 2017-09-14 Basf Se Dérivés spirocycliques
WO2017167832A1 (fr) 2016-04-01 2017-10-05 Basf Se Composés bicycliques
WO2017198588A1 (fr) 2016-05-18 2017-11-23 Basf Se Capsules comprenant des benzylpropargyléthers destinés à être utilisés comme inhibiteurs de nitrification
US9907308B2 (en) 2016-07-13 2018-03-06 Nissan Chemical Industries, Ltd. Aqueous suspension agrochemical composition
WO2018108671A1 (fr) 2016-12-16 2018-06-21 Basf Se Composés pesticides
WO2018162312A1 (fr) 2017-03-10 2018-09-13 Basf Se Dérivés spirocycliques
WO2018166855A1 (fr) 2017-03-16 2018-09-20 Basf Se Dihydroisoxazoles à substitution hétérobicyclique
WO2018177781A1 (fr) 2017-03-28 2018-10-04 Basf Se Composés pesticides
WO2018177970A1 (fr) 2017-03-31 2018-10-04 Basf Se Procédé de préparation de composés chiraux 2,3-dihydrothiazolo[3,2-a]pyrimidin-4-ium
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WO2018206479A1 (fr) 2017-05-10 2018-11-15 Basf Se Composés pesticides bicycliques
US10149477B2 (en) 2014-10-06 2018-12-11 Basf Se Substituted pyrimidinium compounds for combating animal pests
WO2018224455A1 (fr) 2017-06-07 2018-12-13 Basf Se Dérivés de cyclopropyle substitués
WO2018229202A1 (fr) 2017-06-16 2018-12-20 Basf Se Composés imidazolium mésoioniques et leurs dérivés destinés à être utilisés pour lutter contre des animaux nuisibles
WO2018234202A1 (fr) 2017-06-19 2018-12-27 Basf Se Composés pyrimidinium substitués et dérivés destinés à lutter contre les animaux nuisibles
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EP3453706A1 (fr) 2017-09-08 2019-03-13 Basf Se Composés pesticides de l'imizazole
WO2019072906A1 (fr) 2017-10-13 2019-04-18 Basf Se Composés d'imidazolidine pyrimidinium pour lutter contre des animaux nuisibles
WO2019121143A1 (fr) 2017-12-20 2019-06-27 Basf Se Dérivés de cyclopropyle substitués
WO2019121159A1 (fr) 2017-12-21 2019-06-27 Basf Se Composés pesticides
WO2019137995A1 (fr) 2018-01-11 2019-07-18 Basf Se Nouveaux composés pyridazine destinés à la lutte contre les nuisibles invertébrés
WO2019145140A1 (fr) 2018-01-09 2019-08-01 Basf Se Composés silyléthynyle hétaryle à utiliser en tant qu'inhibiteurs de nitrification
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WO2019156903A1 (fr) 2018-02-12 2019-08-15 Fmc Corporation Composés d'isoxazoline naphtalène destinés à la lutte contre les nuisibles invertébrés
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WO2019166558A1 (fr) 2018-02-28 2019-09-06 Basf Se Utilisation d'éthers de pyrazole propargyle comme inhibiteurs de nitrification
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WO2019175713A1 (fr) 2018-03-14 2019-09-19 Basf Corporation Nouvelles molécules de catéchol et leur utilisation en tant qu'inhibiteurs de voies métaboliques associées à p450
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WO2019219529A1 (fr) 2018-05-15 2019-11-21 Basf Se Mélanges comprenant du benzpyrimoxan et de l'oxazosulfyle et utilisations et leurs procédés d'application
WO2019224092A1 (fr) 2018-05-22 2019-11-28 Basf Se Dérivés c15 à action pesticide de ginkgolides
WO2020002472A1 (fr) 2018-06-28 2020-01-02 Basf Se Utilisation d'alkynylthiophènes en tant qu'inhibiteurs de nitrification
WO2020020777A1 (fr) 2018-07-23 2020-01-30 Basf Se Utilisation de 2-thiazolines substituées en tant qu'inhibiteurs de nitrification
WO2020020765A1 (fr) 2018-07-23 2020-01-30 Basf Se Utilisation d'un composé de thiazolidine substitué en tant qu'inhibiteur de nitrification
US10556844B2 (en) 2015-02-06 2020-02-11 Basf Se Pyrazole compounds as nitrification inhibitors
EP3613736A1 (fr) 2018-08-22 2020-02-26 Basf Se Dérivés de glutarimide substitués
EP3628156A1 (fr) 2018-09-28 2020-04-01 Basf Se Procede de lutte contre les ravageurs de la canne a sucre, des agrumes, du colza et des plants de pomme de terre
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JP2021501755A (ja) * 2017-11-07 2021-01-21 インターベット インターナショナル ベー． フェー． 大きいサイズのイソキサゾリン粒子の調製方法
EP3769623A1 (fr) 2019-07-22 2021-01-27 Basf Se Composés et dérivés mésoioniques d'imidazolium pour lutter contre les animaux nuisibles
JP2021506855A (ja) * 2017-12-19 2021-02-22 シンジェンタ パーティシペーションズ アーゲー 多形
US11053175B2 (en) 2015-05-12 2021-07-06 Basf Se Thioether compounds as nitrification inhibitors
US11142514B2 (en) 2015-10-02 2021-10-12 Basf Se Imino compounds with a 2-chloropyrimidin-5-yl substituent as pest-control agents
WO2022167488A1 (fr) 2021-02-02 2022-08-11 Basf Se Action synergique de dcd et d'alcoxypyrazoles en tant qu'inhibiteurs de nitrification
WO2022243521A1 (fr) 2021-05-21 2022-11-24 Basf Se Utilisation de composés d'éthynylpyridine en tant qu'inhibiteurs de nitrification
WO2022243523A1 (fr) 2021-05-21 2022-11-24 Basf Se Utilisation d'un composé alcoxy pyrazole n-fonctionnalisé en tant qu'inhibiteur de nitrification
WO2022268810A1 (fr) 2021-06-21 2022-12-29 Basf Se Réseaux organométalliques à blocs de construction à base de pyrazole
WO2023203066A1 (fr) 2022-04-21 2023-10-26 Basf Se Action synergique en tant qu'inhibiteurs de nitrification d'oligomères de dicyandiamide (dcd) avec l'alcoxypyrazole et ses oligomères
WO2024028243A1 (fr) 2022-08-02 2024-02-08 Basf Se Composés pesticides pyrazolo

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115385866A (zh) * 2021-05-24 2022-11-25 洛阳惠中兽药有限公司 氟雷拉纳晶型及其制备方法与应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01121273A (ja) * 1987-11-05 1989-05-12 Nippon Chemiphar Co Ltd ベンズイミダゾール誘導体の多形体
JPH10236827A (ja) * 1996-12-25 1998-09-08 Nippon Kayaku Co Ltd シスプラチン微粉末及びその製造方法
WO2007026965A1 (fr) * 2005-09-02 2007-03-08 Nissan Chemical Industries, Ltd. Composé de benzamide à substitution isoxazoline et agent de lutte contre les organismes nuisibles
JP2008236911A (ja) * 2007-03-20 2008-10-02 Nidec Copal Corp 表面実装用振動モータ
JP2008285445A (ja) * 2007-05-18 2008-11-27 Hidekazu Takada 塩酸サルポグレラートの工業的製造方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008239611A (ja) * 2007-02-27 2008-10-09 Nissan Chem Ind Ltd イソキサゾリン置換ベンズアミド化合物及び有害生物防除剤
US8053452B2 (en) * 2007-06-29 2011-11-08 Nissan Chemical Industries, Ltd. Substituted isoxazoline or enone oxime compound, and pest control agent
WO2010005048A1 (fr) * 2008-07-09 2010-01-14 日産化学工業株式会社 Procédé de production d’un composé amide de l’acide benzoïque à substitution isoxazoline
DK2576523T3 (en) * 2010-05-27 2016-04-18 Du Pont A crystalline form of 4- [5- [3-chloro-5- (trifluoromethyl) phenyl] -4,5-dihydro-5- (trifluoromethyl) -3-isoxazolyl] -N- [2-oxo-2 - [( 2,2,2-trifluoroethyl) amino] ethyl] - 1-naphthalenecarboxamide

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01121273A (ja) * 1987-11-05 1989-05-12 Nippon Chemiphar Co Ltd ベンズイミダゾール誘導体の多形体
JPH10236827A (ja) * 1996-12-25 1998-09-08 Nippon Kayaku Co Ltd シスプラチン微粉末及びその製造方法
WO2007026965A1 (fr) * 2005-09-02 2007-03-08 Nissan Chemical Industries, Ltd. Composé de benzamide à substitution isoxazoline et agent de lutte contre les organismes nuisibles
JP2008236911A (ja) * 2007-03-20 2008-10-02 Nidec Copal Corp 表面実装用振動モータ
JP2008285445A (ja) * 2007-05-18 2008-11-27 Hidekazu Takada 塩酸サルポグレラートの工業的製造方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
C.G.WERMUTH, SAISHIN SOYAKU KAGAKU, LAST VOLUME, 25 September 1999 (1999-09-25), TECHNOMICS, INC., pages 452 - 453 *
TEISUKE OKANO: "Shin ? Yakuzaigaku Soron, revised 3rd edition", SHIN . YAKUZAIGAKU SORON, vol. 3RD, 10 April 1987 (1987-04-10), NANKODO CO., LTD.,, pages 26, 111, 256, 257 *

Cited By (85)

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WO2015115488A1 (fr) * 2014-01-31 2015-08-06 日産化学工業株式会社 Composition de pesticide liquide
US10149477B2 (en) 2014-10-06 2018-12-11 Basf Se Substituted pyrimidinium compounds for combating animal pests
WO2016071499A1 (fr) 2014-11-06 2016-05-12 Basf Se Composé hétérobicyclique de 3-pyridyle utilisé pour lutter contre les invertébrés nuisibles
US10556844B2 (en) 2015-02-06 2020-02-11 Basf Se Pyrazole compounds as nitrification inhibitors
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US10701937B2 (en) 2015-02-11 2020-07-07 Basf Se Pesticidal mixture comprising a pyrazole compound, an insecticide and a fungicide
WO2016162371A1 (fr) 2015-04-07 2016-10-13 Basf Agrochemical Products B.V. Utilisation d'un composé de carboxamide insecticide contre les nuisibles sur des plantes cultivées
US11053175B2 (en) 2015-05-12 2021-07-06 Basf Se Thioether compounds as nitrification inhibitors
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US11142514B2 (en) 2015-10-02 2021-10-12 Basf Se Imino compounds with a 2-chloropyrimidin-5-yl substituent as pest-control agents
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WO2017153217A1 (fr) 2016-03-09 2017-09-14 Basf Se Dérivés spirocycliques
WO2017153218A1 (fr) 2016-03-11 2017-09-14 Basf Se Procédé pour lutter contre des organismes nuisibles aux végétaux
WO2017167832A1 (fr) 2016-04-01 2017-10-05 Basf Se Composés bicycliques
WO2017198588A1 (fr) 2016-05-18 2017-11-23 Basf Se Capsules comprenant des benzylpropargyléthers destinés à être utilisés comme inhibiteurs de nitrification
US9907308B2 (en) 2016-07-13 2018-03-06 Nissan Chemical Industries, Ltd. Aqueous suspension agrochemical composition
WO2018108671A1 (fr) 2016-12-16 2018-06-21 Basf Se Composés pesticides
JP2020504116A (ja) * 2016-12-22 2020-02-06 シンジェンタ パーティシペーションズ アーゲー 多形
KR20190097101A (ko) * 2016-12-22 2019-08-20 신젠타 파티서페이션즈 아게 다형체
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WO2018162312A1 (fr) 2017-03-10 2018-09-13 Basf Se Dérivés spirocycliques
WO2018166855A1 (fr) 2017-03-16 2018-09-20 Basf Se Dihydroisoxazoles à substitution hétérobicyclique
WO2018177781A1 (fr) 2017-03-28 2018-10-04 Basf Se Composés pesticides
EP3978504A1 (fr) 2017-03-31 2022-04-06 Basf Se Dérivés chiraux de 2,3-dihydrothiazolo[3,2-a]pyrimidine pour lutter contre des animaux nuisibles
WO2018177970A1 (fr) 2017-03-31 2018-10-04 Basf Se Procédé de préparation de composés chiraux 2,3-dihydrothiazolo[3,2-a]pyrimidin-4-ium
WO2018192793A1 (fr) 2017-04-20 2018-10-25 Basf Se Dérivés de rhodanine substitués
WO2018197466A1 (fr) 2017-04-26 2018-11-01 Basf Se Dérivés de succinimide substitués utilisés en tant que pesticides
WO2018206479A1 (fr) 2017-05-10 2018-11-15 Basf Se Composés pesticides bicycliques
WO2018224455A1 (fr) 2017-06-07 2018-12-13 Basf Se Dérivés de cyclopropyle substitués
WO2018229202A1 (fr) 2017-06-16 2018-12-20 Basf Se Composés imidazolium mésoioniques et leurs dérivés destinés à être utilisés pour lutter contre des animaux nuisibles
WO2018234202A1 (fr) 2017-06-19 2018-12-27 Basf Se Composés pyrimidinium substitués et dérivés destinés à lutter contre les animaux nuisibles
WO2018234488A1 (fr) 2017-06-23 2018-12-27 Basf Se Dérivés de cyclopropyle substitués
WO2019042932A1 (fr) 2017-08-31 2019-03-07 Basf Se Procédé de lutte contre les parasites du riz dans le riz
WO2019043183A1 (fr) 2017-08-31 2019-03-07 Basf Se Procédé de lutte contre les nuisibles du riz dans le riz
EP3453706A1 (fr) 2017-09-08 2019-03-13 Basf Se Composés pesticides de l'imizazole
WO2019072906A1 (fr) 2017-10-13 2019-04-18 Basf Se Composés d'imidazolidine pyrimidinium pour lutter contre des animaux nuisibles
US11858904B2 (en) 2017-11-07 2024-01-02 Intervet Inc. Process for preparing large size isoxazoline particles
JP7446222B2 (ja) 2017-11-07 2024-03-08 インターベット インターナショナル ベー． フェー． 大きいサイズのイソキサゾリン粒子の調製方法
JP2021501755A (ja) * 2017-11-07 2021-01-21 インターベット インターナショナル ベー． フェー． 大きいサイズのイソキサゾリン粒子の調製方法
JP2021506855A (ja) * 2017-12-19 2021-02-22 シンジェンタ パーティシペーションズ アーゲー 多形
WO2019121143A1 (fr) 2017-12-20 2019-06-27 Basf Se Dérivés de cyclopropyle substitués
WO2019121159A1 (fr) 2017-12-21 2019-06-27 Basf Se Composés pesticides
WO2019145140A1 (fr) 2018-01-09 2019-08-01 Basf Se Composés silyléthynyle hétaryle à utiliser en tant qu'inhibiteurs de nitrification
WO2019137995A1 (fr) 2018-01-11 2019-07-18 Basf Se Nouveaux composés pyridazine destinés à la lutte contre les nuisibles invertébrés
WO2019156903A1 (fr) 2018-02-12 2019-08-15 Fmc Corporation Composés d'isoxazoline naphtalène destinés à la lutte contre les nuisibles invertébrés
WO2019166561A1 (fr) 2018-02-28 2019-09-06 Basf Se Utilisation d'alkoxypyrazoles comme inhibiteurs de nitrification
WO2019166558A1 (fr) 2018-02-28 2019-09-06 Basf Se Utilisation d'éthers de pyrazole propargyle comme inhibiteurs de nitrification
WO2019166560A1 (fr) 2018-02-28 2019-09-06 Basf Se Utilisation de composés alcoxy pyrazole n-fonctionnalisés en tant qu'inhibiteurs de nitrification
WO2019175712A1 (fr) 2018-03-14 2019-09-19 Basf Corporation Nouvelles utilisations de molécules de catéchol en tant qu'inhibiteurs de voies métaboliques de glutathion s-transférase
WO2019175713A1 (fr) 2018-03-14 2019-09-19 Basf Corporation Nouvelles molécules de catéchol et leur utilisation en tant qu'inhibiteurs de voies métaboliques associées à p450
WO2019185413A1 (fr) 2018-03-27 2019-10-03 Basf Se Dérivés de cyclopropyle substitués pesticides
WO2019219529A1 (fr) 2018-05-15 2019-11-21 Basf Se Mélanges comprenant du benzpyrimoxan et de l'oxazosulfyle et utilisations et leurs procédés d'application
WO2019224092A1 (fr) 2018-05-22 2019-11-28 Basf Se Dérivés c15 à action pesticide de ginkgolides
WO2020002472A1 (fr) 2018-06-28 2020-01-02 Basf Se Utilisation d'alkynylthiophènes en tant qu'inhibiteurs de nitrification
WO2020020777A1 (fr) 2018-07-23 2020-01-30 Basf Se Utilisation de 2-thiazolines substituées en tant qu'inhibiteurs de nitrification
WO2020020765A1 (fr) 2018-07-23 2020-01-30 Basf Se Utilisation d'un composé de thiazolidine substitué en tant qu'inhibiteur de nitrification
EP3613736A1 (fr) 2018-08-22 2020-02-26 Basf Se Dérivés de glutarimide substitués
EP3628156A1 (fr) 2018-09-28 2020-04-01 Basf Se Procede de lutte contre les ravageurs de la canne a sucre, des agrumes, du colza et des plants de pomme de terre
WO2020064480A1 (fr) 2018-09-28 2020-04-02 Basf Se Mélange pesticide comprenant un composé mésoionique et un biopesticide
WO2020064408A1 (fr) 2018-09-28 2020-04-02 Basf Se Procédé de lutte contre les insectes résistants aux insecticides et la transmission de virus aux plantes
EP3628158A1 (fr) 2018-09-28 2020-04-01 Basf Se Composé pesticide contenant des substances mésoioniques et des biopesticides
WO2020064492A1 (fr) 2018-09-28 2020-04-02 Basf Se Procédé de régulation des nuisibles par application de traitement de semences d'un composé mésoionique ou d'un mélange de ceux-ci
EP3628157A1 (fr) 2018-09-28 2020-04-01 Basf Se Procede de lutte contre les insectes resistants aux insecticides et transmission du virus aux plantes
EP3643705A1 (fr) 2018-10-24 2020-04-29 Basf Se Composés pesticides
WO2020083733A1 (fr) 2018-10-24 2020-04-30 Basf Se Composés pesticides
WO2020109039A1 (fr) 2018-11-28 2020-06-04 Basf Se Composés pesticides
WO2020126591A1 (fr) 2018-12-18 2020-06-25 Basf Se Composés de pyrimidinium substitués utilisables dans le cadre de la lutte contre les animaux nuisibles
EP3696177A1 (fr) 2019-02-12 2020-08-19 Basf Se Composés hétérocycliques destinés à la lutte contre les organismes nuisibles invertébrés
WO2020239517A1 (fr) 2019-05-29 2020-12-03 Basf Se Composés imidazolium mésoioniques et leurs dérivés pour lutter contre les animaux nuisibles
WO2021013561A1 (fr) 2019-07-19 2021-01-28 Basf Se Dérivés pyrazolés et triazolés antiparasitaires
EP3766879A1 (fr) 2019-07-19 2021-01-20 Basf Se Dérivés de pytazole pesticides
EP3769623A1 (fr) 2019-07-22 2021-01-27 Basf Se Composés et dérivés mésoioniques d'imidazolium pour lutter contre les animaux nuisibles
WO2022167488A1 (fr) 2021-02-02 2022-08-11 Basf Se Action synergique de dcd et d'alcoxypyrazoles en tant qu'inhibiteurs de nitrification
WO2022243523A1 (fr) 2021-05-21 2022-11-24 Basf Se Utilisation d'un composé alcoxy pyrazole n-fonctionnalisé en tant qu'inhibiteur de nitrification
WO2022243521A1 (fr) 2021-05-21 2022-11-24 Basf Se Utilisation de composés d'éthynylpyridine en tant qu'inhibiteurs de nitrification
WO2022268810A1 (fr) 2021-06-21 2022-12-29 Basf Se Réseaux organométalliques à blocs de construction à base de pyrazole
WO2023203066A1 (fr) 2022-04-21 2023-10-26 Basf Se Action synergique en tant qu'inhibiteurs de nitrification d'oligomères de dicyandiamide (dcd) avec l'alcoxypyrazole et ses oligomères
WO2024028243A1 (fr) 2022-08-02 2024-02-08 Basf Se Composés pesticides pyrazolo

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